Membrane damaging activity of a maslinic acid analog.

Close inspection of human ovarian cancer cells A2780 in the course of an antitumor screening using maslinic acid analogs revealed for one of the compounds, 4-oxa-4-phenyl-butyl 2,3-dihydroxy-olean-12-en-28-oate (1), an unusual behavior. During the incubation of the cells with 1, at the perimeter of the cells or close by crystals were formed consisting of cholesterol and excess 1. Compound 1 was incorporated into the cell's membrane followed by an extrusion of cholesterol from the lipid rafts. As a consequence of the alterations of the cell membrane, a volume decrease was initiated that triggered apoptosis; this extends previous models on apoptosis initiating mechanisms.